Stereoselective Aldol Condensations via Boron Enolates. The Syntheses of (+)-Prelog-Djerassi Lactone and (+)-Tylonolide

Citation

Bartroli, Javier Francisco (1984) Stereoselective Aldol Condensations via Boron Enolates. The Syntheses of (+)-Prelog-Djerassi Lactone and (+)-Tylonolide. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/3v27-xh37. https://resolver.caltech.edu/CaltechTHESIS:11092018-094859390

Abstract

The use of boron enolates of chiral N-acyl oxazolidinones i and ii in highly stereoselective aldol condensations is described. Mild base hydrolysis of the products affords optically pure erythro β-hydroxy acids and the chiral auxiliary, which can be reconverted into i or ii in one step.

The utility and scope of these reactions is demonstrated by the total syntheses of (+)-Prelog-Djerassi lactone and (+)-Tylonolide, cyclic 5,20-hemiacetal .

[Chemical structures included in scanned thesis' abstract, p. v.]

Thesis Files